Compound and organic light-emitting device including the same

ABSTRACT

A compound represented by Formula 1 or Formula 2, and an organic light-emitting device including a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and the compound represented by Formula 1 or Formula 2.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2015-0018130, filed on Feb. 5, 2015, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND

1. Field

One or more aspects of embodiments of the present invention relate to acompound and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that have wideviewing angles, high contrast ratios, short response times, andexcellent brightness, driving voltage, and response speedcharacteristics, and can produce full-color images.

The organic light-emitting device may include a first electrodepositioned on a substrate, and a hole transport region, an emissionlayer, an electron transport region, and a second electrode,sequentially positioned on the first electrode. Holes provided from thefirst electrode may move toward the emission layer through the holetransport region, and electrons provided from the second electrode maymove toward the emission layer through the electron transport region.Carriers (e.g., holes and electrons), are then recombined in theemission layer to produce excitons. These excitons change from anexcited state to a ground state, thereby generating light.

SUMMARY

One or more aspects of embodiments of the present invention relate to acompound having an excellent electron transport capability and anorganic light-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to one or more embodiments of the present invention, providedis a compound represented by Formula 1 or Formula 2:

wherein in Formulae 1 and 2,

R₁ to R₄ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—P(═O)R₁₁R₁₂, and —P(═S)R₁₃R₁₄;

L₁ to L₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

X₁ to X₁₂ may be each independently CR₂₁ or N;

at least one selected from X₁ to X₁₂ may be N;

R₁₁ to R₁₄, and R₂₁ may be each independently selected from asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;

l, m, n, and o may be each independently an integer selected from 1 to5;

a1, a2, a3, and a4 may be each independently an integer selected from 0to 3;

when a1, a2, a3, and a4 are each independently 2 or more, respective L₁sto L₄s may be each independently identical to or different from eachother; and

at least one of substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group,substituted monovalent non-aromatic condensed heteropolycyclic group,C₃-C₁₀ cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylenegroup, substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, and substituted divalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₁-C₆₀ alkynyl group, a C₂-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅) and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

In one or more embodiments of the present invention, an organiclight-emitting device includes: a first electrode; a second electrodefacing the first electrode; and an organic layer between the firstelectrode and the second electrode, the organic layer including anemission layer, wherein the organic layer includes one of compoundsrepresented by any one of Formulae 1 and 2.

In one or more embodiments of the present invention, a flat paneldisplay apparatus includes the organic light-emitting device, whereinthe first electrode of the organic light-emitting device is electricallyconnected to a source electrode or a drain electrode of a thin filmtransistor.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawing, which is a schematic view ofan organic light-emitting device according to one or more embodiments ofthe present invention.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawing, wherein likereference numerals refer to like elements throughout. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the present embodiments are merely described below, byreferring to the drawing, to explain aspects of the present description.

According to one or more embodiments of the present invention, acompound is represented by Formula 1 or Formula 2:

In Formulae 1 and 2,

R₁ to R₄ may be each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—P(═O)R₁₁R₁₂, and —P(═S)R₁₃R₁₄;

L₁ to L₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

X₁ to X₁₂ may be each independently CR₂₁ or N;

at least one selected from X₁ to X₁₂ may be N;

R₁₁ to R₁₄, and R₂₁ may be each independently selected from asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;

l, m, n, and o may be each independently an integer selected from 1 to5;

a1, a2, a3, and a4 may be each independently an integer selected from 0to 3; and

when a1, a2, a3, and a4 are each independently 2 or more, respective L₁sto L₄s may be each independently identical to or different from eachother; and

at least one of substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group,substituted monovalent non-aromatic condensed heteropolycyclic group,C₃-C₁₀ cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylenegroup, substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, and substituted divalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₂-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₂-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅) and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

For example, to facilitate stability with respect to electrons andelectron movement speed characteristics, an organic mono-molecularmaterial selected from organometallic complexes may be used as anelectron transport material. From among such materials, Alq3 is known inthe art to have high stability and electron affinity. However, when Alq3is used in a blue light-emitting device, color purity may deterioratedue to exciton diffusion-derived emission.

Flavone derivatives and a germanium and silicon chloropentadienederivatives are also known in the art.

Examples of the organic mono-molecular material include a2-biphenyl-4-yl-5-(4-t-butylphenyl)-1,3,4-oxadiazole (Butyl-PBD)derivative linked to a spiro compound, and2,2′,2″-(benzene-1,3,5-triyl)-tris(1-phenyl-1H-benzimidazole) (TPBI)having both a hole blocking capability and an excellent electrontransport capability.

In addition, benzoimidazole derivatives are known in the art to haveexcellent durability.

However, an organic light-emitting device including an electrontransport layer having the organic mono-molecular material as describedabove has a relatively short emission lifespan, and low preservativedurability and reliability, which may stem from physical or chemicalchange, and photochemical or electrochemical change of an organicmaterial, oxidation of an electrode, exfoliation, or lack of durabilityof the organic material.

In contrast, a compound represented by Formula 1 or Formula 2 accordingto one or more embodiments of the present invention has excellentelectron transport capability.

Accordingly, an organic light-emitting device including the compoundaccording to one or more embodiments of the present invention exhibitshigh efficiency, low voltage, high luminance, and long lifespan duringdriving (or operation).

Hereinafter, substituents of Formula 1 and Formula 2 are described inmore detail.

In some embodiments, at least one selected from X₁ to X₆ in Formula 1may be N. For example, in Formula 1, only X₁ may be N, only X₆ may be N,or both X₁ and X₆ may be N.

In some embodiments, Formula 1 may be represented by Formula 3 below:

In some embodiments, Formula 1 may be represented by Formula 4 below:

In some embodiments, Formula 2 may be represented by Formula 5 below:

Regarding Formulae 3 to 5, definitions of substituents are the same asprovided above.

In some embodiments, R₁ to R₄ may be each independently selected fromhydrogen, deuterium, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.

In some embodiments, R₁ to R₄ in Formula 1 may be each independentlyselected from hydrogen, deuterium, a phenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a furinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group; and

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, afurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.

In some embodiments, L₁ to L₄ may be each independently selected from asubstituted or unsubstituted C₆-C₆₀ arylene group, a substituted orunsubstituted C₁-C₆₀ heteroarylene group, a substituted or unsubstituteddivalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group.

In some embodiments, L₁ to L₄ may be each independently selected from aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a furinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a furinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group,eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a pherylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.

In some embodiments, R₁ to R₄ may be each independently selected fromhydrogen, deuterium, and groups represented by Formulae 2a to 2f:

In Formulae 2a to 2f, H₁ is NR₂₁, O, or S.

R₁₁, R₁₂, R₂₁, Z₁, and Z₂ may be each independently selected fromhydrogen atom, deuterium, a halogen group, a cyano group, a nitro group,a hydroxyl group, a carboxyl group, a substituted or unsubstitutedC₁-C₂₀ alkyl group, a substituted or unsubstituted C₆-C₂₀ aryl group, asubstituted or unsubstituted C₁-C₂₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group;

p is an integer of 1 to 9, and when p is two or more, the plurality ofZ₁(s) may be identical to or different from each other; and

* indicates a binding site.

In some embodiments, L₁ to L₄ may be each independently selected fromgroups represented by Formulae 3a to 3c:

In Formulae 3a to 3c, Z₁ may be selected from hydrogen atom, deuterium,a halogen group, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, a substituted orunsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;and * indicates a binding site.

In some embodiments, the compound of Formulae 1 or 2 may be any one ofcompounds illustrated below:

The term “organic layer” used herein refers to a single layer and/or aplurality of layers between the first electrode and the second electrodeof an organic light-emitting device. A material included in the “organiclayer” is not limited to an organic material.

The drawing is a schematic view of an organic light-emitting device 10according to one or more embodiments of the present invention. Theorganic light-emitting device 10 includes a first electrode 110, anorganic layer 150, and a second electrode 190.

Hereinafter, the structure of an organic light-emitting device accordingto one or more embodiments and a method of manufacturing an organiclight-emitting device according to one or more embodiments of thepresent invention will be described in connection with the drawing.

In the drawing, a substrate may be additionally positioned under thefirst electrode 110 or above the second electrode 190. The substrate maybe a glass substrate or transparent plastic substrate, each withexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and/or water-resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode on the substrate. When thefirst electrode 110 is an anode, the material for the first electrode110 may be selected from materials with a high work function so as tomake holes be easily injected. The first electrode 110 may be areflective electrode or a transmissive electrode. The material for thefirst electrode 110 may be a transparent and highly conductive material,and non-limiting examples of such material include indium tin oxide(ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO).When the first electrode 110 is a semi-transmissive electrode or areflective electrode, as a material for forming the first electrode, atleast one of magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li),calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag) maybe used (utilized).

The first electrode 110 may have a single-layer structure, or amulti-layer structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

An organic layer 150 is positioned on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode and the emission layer, and an electrontransport region between the emission layer and the second electrode.

In some embodiments, the hole transport region may include at least oneselected from a hole transport layer (HTL), a hole injection layer(HIL), a buffer layer, and an electron blocking layer, and an electrontransport region may include at least one selected from a hole blockinglayer (HBL), an electron transport layer (ETL), and an electroninjection layer (EIL). However, embodiments of the present invention arenot limited thereto.

The hole transport region may have a single-layered structure formed ofa single material, a single-layered structure formed of a plurality ofdifferent materials, or a multi-layered structure having a plurality oflayers formed of a plurality of different materials.

For example, the hole transport region may have a single-layeredstructure formed of a plurality of different materials, or a structureof hole injection layer/hole transport layer, a structure of holeinjection layer/hole transport layer/buffer layer, a structure of holeinjection layer/buffer layer, a structure of hole transport layer/bufferlayer, or a structure of hole injection layer/hole transportlayer/electron blocking layer, wherein the layers of each structure aresequentially stacked from the first electrode 110 in the stated order,but the structure of the hole transport region is not limited thereto.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 110 by using(utilizing) one or more suitable methods, such as vacuum deposition,spin coating casting, a Langmuir-Blodgett (LB) method, ink-jet printing,laser-printing, and/or laser-induced thermal imaging.

When a hole injection layer is formed by vacuum deposition, for example,the vacuum deposition may be performed at a deposition temperature ofabout 100 to about 500° C., at a vacuum degree of about 10⁻⁸ to about10⁻³ torr, and at a deposition rate of about 0.01 to about 100 Å/secdepending on the compound for forming the hole injection layer to bedeposited, and the structure of the hole injection layer to be formed.

When a hole injection layer is formed by spin coating, the spin coatingmay be performed at a coating rate of about 2000 rpm to about 5000 rpm,and at a temperature of about 80° C. to 200° C. depending on thecompound for forming the hole injection layer to be deposited, and thestructure of the hole injection layer to be formed.

When the hole transport region includes a hole transport layer, the holetransport layer may be formed on the first electrode 110 or the holeinjection layer by using (utilizing) one or more suitable methods, suchas vacuum deposition, spin coating, casting, a LB method, ink-jetprinting, laser-printing, and/or laser-induced thermal imaging. When thehole transport layer is formed by vacuum deposition and/or spin coating,deposition and coating conditions for the hole transport layer may bethe same as (or similar to) the deposition and coating conditions forthe hole injection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently understood by referring to thedescription provided herein in connection with L₁;

xa1 to xa4 may be each independently selected from 0, 1, 2, and 3;

xa5 may be selected from 1, 2, 3, 4, and 5; and

R₂₀₁ to R₂₀₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

xa1 to xa4 may be each independently 0, 1, or 2;

xa5 may be 1, 2, or 3;

R₂₀₁ ^(to) R₂₀₄ are each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an azulenyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, but embodiments of the presentinvention are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

For example, the compound represented by Formula 201 may be representedby Formula 201A-1 below, but is not limited thereto:

For example, the compound represented by Formula 202 may be representedby Formula 202A below, but is not limited thereto:

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ in Formulae 201A, 201A-1and 202A are as described above, and R₂₁₁ may be understood by referringto the description provided herein in connection with R₂₀₃, and R₂₁₃ toR₂₁₆ may be each independently selected from hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulae 201A, 201A-1, and 202A,

L₂₀₁ to L₂₀₃ may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, and a triazinylenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

xa1 to xa3 may be each independently 0 or 1;

R₂₀₃, R₂₁₁, and R₂₁₂ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

R₂₁₃ and R₂₁₄ may be each independently selected from:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

R₂₁₅ and R₂₁₆ are each independently selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

xa5 is 1 or 2.

R₂₁₃ and R₂₁₄ in Formulae 201A, and 201A-1 may bind to each other toform a saturated or unsaturated ring.

The compound represented by Formula 201, and the compound represented byFormula 202 may each independently include any one of compounds HT1 toHT20 illustrated below, but are not limited thereto.

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes both a hole injection layer and a holetransport layer, a thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, for example, about 100 Å toabout 1,000 Å, and a thickness of the hole transport layer may be in arange of about 50Å to about 2,000 Å, for example about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer, and the hole transport layer are within any of theseranges, satisfactory hole transporting characteristics may be obtainedwithout a substantial increase in driving voltage.

The hole transport region may further include, in addition to theabove-described materials, a charge-generation material for improvementof conductive properties. The charge-generation material may behomogeneously or unhomogeneously dispersed in the hole transport region.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments of the presentinvention are not limited thereto. Non-limiting examples of the p-dopantinclude a quinone derivative, such as tetracyanoquinonedimethane (TCNQ)and/or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane(F4-TCNQ); a metal oxide, such as a tungsten oxide and/or a molybdenumoxide, and Compound HT-D1 illustrated below.

The hole transport region may further include a buffer layer, inaddition to an electron blocking layer, a hole injection layer, and ahole transport layer. Since the buffer layer may compensate for anoptical resonance distance according to a wavelength of light emittedfrom the emission layer, light-emission efficiency of the formed organiclight-emitting device may be improved. For use as a material included inthe buffer layer, materials that are included in the hole transportregion may be used. The electron blocking layer prevents (orsubstantially blocks) the injection of electrons from the electrontransport region.

An emission layer is formed on the first electrode 110 or the holetransport region by using (utilizing) one or more suitable methods, suchas vacuum deposition, spin coating, casting, a LB method, ink-jetprinting, laser-printing, and/or laser-induced thermal imaging. When theemission layer is formed by vacuum deposition and/or spin coating,deposition and coating conditions for the emission layer may be the sameas (or similar to) those for the hole injection layer.

When the organic light-emitting device 10 is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to (or as defined by) a sub pixel. In some embodiments, theemission layer may have a stacked structure of a red emission layer, agreen emission layer, and a blue emission layer, or may include ared-light emission material, a green-light emission material, and ablue-light emission material, which are mixed with each other in asingle layer, to emit white light.

The emission layer may include a host and a dopant.

For example, the host may include at least one selected from TPBi,TBADN, ADN (herein also referred to as “DNA”), CBP, CDBP, and TCP:

In some embodiments, the host may include a compound represented byFormula 301 below.

Ar₃₀₁—[(L₃₀₁)_(xb1)—R₃₀₁]_(xb2).   Formula 301

In Formula 301,

Ar₃₀₁ may be selected from:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene; and

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (where Q₃₀₁ to Q₃₀₃ may be each independentlyselected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group);

a description of L₃₀₁ may be understood by referring to the descriptionprovided herein in connection with L₂₀₁;

R₃₀₁ may be selected from:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group; and

xb1 may be selected from 0, 1, 2, and 3;

xb2 may be selected from 1, 2, 3, and 4.

For example, in Formula 301,

L₃₀₁ may be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

R₃₀₁ may be selected from:

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, and a chrysenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and achrysenyl group, but embodiments of the present invention are notlimited thereto.

For example, the host may include a compound represented by Formula 301Abelow:

Descriptions of substituents of Formula 301A may be understood byreferring to the corresponding descriptions provided herein.

The compound represented by Formula 301 may include at least one ofCompounds H1 to H42, but is not limited thereto:

In some embodiments, the host may include at least one of Compounds H43to H49 below, but is not limited thereto:

The dopant may include at least one selected from a fluorescent dopantand a phosphorescent dopant.

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:

In Formula 401,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

X₄₀₁ to X₄₀₄ may be each independently nitrogen or carbon;

A₄₀₁ and A₄₀₂ rings may be each independently selected from asubstituted or unsubstituted benzene, a substituted or unsubstitutednaphthalene, a substituted or unsubstituted fluorene, a substituted orunsubstituted spiro-fluorene, a substituted or unsubstituted indene, asubstituted or unsubstituted pyrrole, a substituted or unsubstitutedthiophene, a substituted or unsubstituted furan, a substituted orunsubstituted imidazole, a substituted or unsubstituted pyrazole, asubstituted or unsubstituted thiazole, a substituted or unsubstitutedisothiazole, a substituted or unsubstituted oxazole, a substituted orunsubstituted isoxazole, a substituted or unsubstituted pyridine, asubstituted or unsubstituted pyrazine, a substituted or unsubstitutedpyrimidine, a substituted or unsubstituted pyridazine, a substituted orunsubstituted quinoline, a substituted or unsubstituted isoquinoline, asubstituted or unsubstituted benzoquinoline, a substituted orunsubstituted quinoxaline, a substituted or unsubstituted quinazoline, asubstituted or unsubstituted carbazole, a substituted or unsubstitutedbenzoimidazole, a substituted or unsubstituted benzofuran, a substitutedor unsubstituted benzothiophene, a substituted or unsubstitutedisobenzothiophene, a substituted or unsubstituted benzoxazole, asubstituted or unsubstituted isobenzoxazole, a substituted orunsubstituted triazole, a substituted or unsubstituted oxadiazole, asubstituted or unsubstituted triazine, a substituted or unsubstituteddibenzofuran, and a substituted or unsubstituted dibenzothiophene; and

at least one substituent of the substituted benzene, substitutednaphthalene, substituted fluorene, substituted spiro-fluorene,substituted indene, substituted pyrrole, substituted thiophene,substituted furan, substituted imidazole, substituted pyrazole,substituted thiazole, substituted isothiazole, substituted oxazole,substituted isoxazole, substituted pyridine, substituted pyrazine,substituted pyrimidine, substituted pyridazine, substituted quinoline,substituted isoquinoline, substituted benzoquinoline, substitutedquinoxaline, substituted quinazoline, substituted carbazole, substitutedbenzoimidazole, substituted benzofuran, substituted benzothiophene,substituted isobenzothiophene, substituted benzoxazole, substitutedisobenzoxazole, substituted triazole, substituted oxadiazole,substituted triazine, substituted dibenzofuran, and substituteddibenzothiophene may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₄₀₁)(Q₄₀₂), —Si(Q₄₀₃)(Q₄₀₄)(Q₄₀₅), and —B(Q₄₀₆)(Q₄₀₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, and a non-aromatic condensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₄₁₁)(Q₄₁₂),—Si(Q₄₁₃)(Q₄₁₄)(Q₄₁₅) and —B(Q₄₁₆)(Q₄₁₇); and

—N(Q₄₂₁)(Q₄₂₂), —Si(Q₄₂₃)(Q₄₂₄)(Q₄₂₅), and —B(Q₄₂₆)(Q₄₂₇), where Q₄₀₁ toQ₄₀₇, Q₄₁₁ to Q₄₁₇, and Q₄₂₁ to Q₄₂₇ may be defined as Q₁₁ to Q₁₇, Q₂₁to Q₂₇, and Q₃₁ to Q₃₇ are defined herein.

L₄₀₁ is an organic ligand;

xc1 is 1, 2, or 3; and

xc2 is 0, 1, 2, or 3.

L₄₀₁ may be a monovalent, divalent, or trivalent organic ligand. Forexample, L₄₀₁ may be selected from a halogen ligand (for example, Cland/or F), a diketone ligand (for example, acetylacetonate,1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate,and/or hexafluoroacetonate), a carboxylic acid ligand (for example,picolinate, dimethyl-3-pyrazolecarboxylate, and/or benzoate), a carbonmonooxide ligand, an isonitrile ligand, a cyano ligand, and aphosphorous ligand (for example, phosphine, and phosphite), but is notlimited thereto.

When A₄₀₁ in Formula 401 has two or more substituents, the substituentsof A₄₀₁ may bind to each other to form a saturated or unsaturated ring.

When A₄₀₂ in Formula 401 has two or more substituents, the substituentsof A₄₀₂ may bind to each other to form a saturated or unsaturated ring.

When xc1 in Formula 401 is two or more, a plurality of ligands inFormula 401 may be identical to or different from each other. When xc1in Formula 401 is two or more, A₄₀₁ and/or A₄₀₂ of one ligand may berespectively connected to A₄₀₁ and/or A₄₀₂ of other neighboring ligandseither directly (e.g., via a single bond) or with a linker or a linkinggroup (for example, a C₁-C₅ alkylene, —N(R′)— (where R′ may be a C₁-C₁₀alkyl group or a C₆-C₂₀ aryl group) or —C(═O)—) therebetween.

The phosphorescent dopant may include at least one of Compounds PD1 toPD74 below, but is not limited thereto:

In some embodiments, the phosphorescent dopant may include PtOEP:

The fluorescent dopant may include at least one selected from DPVBi,BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

In some embodiments, the fluorescent dopant may include a compoundrepresented by Formula 501 below.

In Formula 501,

Ar₅₀₁ may be selected from:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene;and

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, abenzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (where Q₅₀₁ to Q₅₀₃ may be each independentlyselected from hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group);

Descriptions of L₅₀₁ to L₅₀₃ are the same as the descriptions providedherein in connection with L₂₀₁;

R₅₀₁ and R₅₀₂ may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

xd1 to xd3 may be each independently selected from 0, 1, 2, and 3; and

xb4 may be selected from 1, 2, 3, and 4.

The fluorescent host may include at least one of Compounds FD1 to FD8.

An amount of the dopant in the emission layer may be in a range of about0.01 to about 15 parts by weight based on 100 parts by weight of thehost, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within any of these ranges, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

An electron transport region may be positioned on the emission layer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer (ETL), and an electroninjection layer, but is not limited thereto.

The electron transport region may include the compound of Formulae 1 or2 according to embodiments of the present invention.

When the electron transport region includes a hole blocking layer, thehole blocking layer may be formed on the emission layer by using(utilizing) one or more suitable methods, such as vacuum deposition,spin coating casting, a Langmuir-Blodgett (LB) method, ink-jet printing,laser-printing, and/or laser-induced thermal imaging. When the holeblocking layer is formed by vacuum deposition and/or spin coating,deposition and coating conditions for the hole blocking layer may besimilar to the deposition and coating conditions for the hole injectionlayer.

The hole blocking layer may include, for example, at least one selectedfrom BCP and Bphen, but is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within any of these ranges, thehole blocking layer may have excellent hole blocking characteristicswithout a substantial increase in driving voltage.

For example, the electron transport region may have a structure ofelectron transport layer/electron injection layer or a structure of holeblocking layer/electron transport layer/electron injection layer,wherein the layers of each structure are sequentially stacked from theemission layer in the stated order, but the structure of the electrontransport region is not limited thereto.

According to some embodiments, the organic layer 150 of the organiclight-emitting device includes an electron transport region between theemission layer and the second electrode 190, and the electron transportregion may include an electron transport layer. The electron transportlayer may include the compound of Formulae 1 or 2 according to one ormore embodiments of the present invention. The electron transport layermay include a plurality of layers. For example, the electron transportlayer may include a first electron transport layer and a second electrontransport layer.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within any of theseranges, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) and/orET-D2.

The electron transport region may include an electron injection layerthat facilitates the injection of electrons from the second electrode190.

The electron injection layer may be formed on the electron transportlayer by using one or more suitable methods, such as vacuum deposition,spin coating casting, a LB method, ink-jet printing, laser-printing,and/or laser-induced thermal imaging. When the electron injection layeris formed by vacuum deposition and/or spin coating, deposition andcoating conditions for the electron injection layer may be the same as(or similar to) those for the hole injection layer.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within any of these ranges,the electron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 190 may be positioned on the organic layer 150having the structure as described herein. The second electrode 190 maybe a cathode which is an electron injection electrode, and in thisregard, a material for the second electrode 190 may be selected from ametal, an alloy, an electrically conductive compound, and a mixturethereof, which have a relatively low work function. Non-limitingexamples of the material for the second electrode 190 include lithium(Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium(Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In someembodiments, the material for forming the second electrode 190 may beITO or IZO. The second electrode 190 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode.

In some embodiments, an organic layer may be formed by depositing thecompound according to embodiments of the present invention, or may beformed by using a wet method in which the compound according toembodiments of the present invention is prepared in the form of asolution, which is then used for coating.

The organic light-emitting device according to one or more embodimentsof the present invention may be used (utilized) in various flat paneldisplay apparatuses, such as a passive matrix organic light-emittingdisplay apparatus and/or an active matrix organic light-emitting displayapparatus. For example, when the organic light-emitting device 10 isincluded in an active matrix organic light-emitting display apparatus, afirst electrode 110 positioned on a substrate acts as a pixel electrodeand may be electrically connected to a source electrode or a drainelectrode of a thin film transistor 200. In addition, the organiclight-emitting device may be included in a flat panel display apparatusthat emits light in opposite directions.

Hereinbefore, the organic light-emitting device has been described withreference to the drawing, but embodiments of the present invention arenot limited thereto.

Hereinafter, definitions of substituents of compounds used herein willbe presented (the number of carbon atoms used for each substituent isnot limited, and does not intend to limit properties of the substituent,and unless defined otherwise, the definition of the substituent isconsistent with a general definition thereof).

A C₁-C₆₀ alkyl group used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms inthe main chain, and non-limiting examples thereof include a methylgroup, an ethyl group, a propyl group, an isobutyl group, a sec-butylgroup, a ter-butyl group, a pentyl group, an iso-amyl group, and a hexylgroup. A C₁-C₆₀ alkylene group used herein refers to a divalent grouphaving the same structure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group used herein refers to a monovalent grouprepresented by —OA₁₀₁ (where A₁₀₁ is the C₁-C₆₀ alkyl group), andnon-limited examples thereof include a methoxy group, an ethoxy group,and an isopropyloxy group.

A C₂-C₆₀ alkenyl group used herein refers to a hydrocarbon group havingat least one carbon-carbon double bond at one or more positions along acarbon chain of the C₂-C₆₀ alkyl group (e.g., in the middle or at eitherterminal end of the C₂-C₆₀ alkyl group), and non-limiting examplesthereof include an ethenyl group, a propenyl group, and a butenyl group.A C₂-C₆₀ alkenylene group used herein refers to a divalent group havingthe same structure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group used herein refers to a hydrocarbon group havingone carbon-carbon triple bond at one or more positions along a carbonchain of the C₂-C₆₀ alkyl group (e.g., in the middle or at eitherterminal end of the C₂-C₆₀ alkyl group), and non-limiting examplesthereof include an ethynyl group, and a propynyl group. A C₂-C₆₀alkynylene group used herein refers to a divalent group having the samestructure as the C₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group used herein refers to a monovalent hydrocarbonmonocyclic group having 3 to 10 carbon atoms as ring-forming atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.A C₃-C₁₀ cycloalkylene group used herein refers to a divalent grouphaving the same structure as the C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group used herein refers to a monovalentmonocyclic group having at least one hetero atom selected from N, O, P,and S as a ring-forming atom and 1 to 10 carbon atoms as the remainingring-forming atoms, and non-limiting examples thereof include atetrahydrofuranyl group, and a tetrahydrothiophenyl group. A C₁-C₁₀heterocycloalkylene group used herein refers to a divalent group havingthe same structure as the C₁-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms as ring-forming atoms andat least one double bond in the ring thereof, and does not havearomaticity, and non-limiting examples thereof include a cyclopentenylgroup, a cyclohexenyl group, and a cycloheptenyl group. A C₃-C₁₀cycloalkenylene group used herein refers to a divalent group having thesame structure as the C₃-C₁₀ cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group used herein refers to a monovalentmonocyclic group that has at least one hetero atom selected from N, O,P, and S as a ring-forming atom, 1 to 10 carbon atoms as the remainingring-forming atoms, and at least one double bond in its ring.Non-limiting examples of the C₁-C₁₀ heterocycloalkenyl group include a2,3-hydrofuranyl group and a 2,3-hydrothiophenyl group. A C₁-C₁₀heterocycloalkenylene group used herein refers to a divalent grouphaving the same structure as the C₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms as ring-formingatoms, and a C₆-C₆₀ arylene group used herein refers to a divalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms asring-forming atoms. Non-limiting examples of the C₆-C₆₀ aryl groupinclude a phenyl group, a naphthyl group, an anthracenyl group, aphenanthrenyl group, a pyrenyl group, and a chrysenyl group. When theC₆-C₆₀ aryl group and/or the C₆-C₆₀ arylene group include two or morerings, the rings may be respectively fused to each other.

A C₁-C₆₀ heteroaryl used herein refers to a monovalent group having acarbocyclic aromatic system that has at least one hetero atom selectedfrom N, O, P, and S as a ring-forming atom, and 1 to 60 carbon atoms asthe remaining ring-forming atoms. A C₁-C₆₀ heteroarylene group usedherein refers to a divalent group having a carbocyclic aromatic systemthat has at least one hetero atom selected from N, O, P, and S as aring-forming atom, and 1 to 60 carbon atoms as the remainingring-forming atoms. Non-limiting examples of the C₁-C₆₀ heteroaryl groupinclude a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group. When the C₁-C₆₀ heteroaryl group and/or the C₁-C₆₀heteroarylene group include two or more rings, the rings may berespectively fused to each other.

A C₆-C₆₀ aryloxy group used herein refers to a monovalent grouprepresented by —OA₁₀₂ (where A₁₀₂ is the C₆-C₆₀ aryl group), and aC₆-C₆₀ arylthio group refers to a monovalent group represented by —SA₁₀₃(where A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group used herein refersto a monovalent group that has two or more rings condensed to eachother, only carbon atoms as ring-forming atoms (for example, having 8 to60 carbon atoms), and does not have overall aromaticity. A non-limitingexample of the monovalent non-aromatic condensed polycyclic group is afluorenyl group. A divalent non-aromatic condensed polycyclic group usedherein refers to a divalent group having the same structure as themonovalent non-aromatic condensed polycyclic group.

A monovalent non-aromatic condensed heteropolycyclic group used hereinrefers to a monovalent group that has two or more rings condensed toeach other, has at least one heteroatom selected from N, 0 P, and S as aring forming atom, and carbon atoms as the remaining ring-forming atoms(for example, having 2 to 60 carbon atoms), and does not have overallaromaticity. A non-limiting example of the monovalent non-aromaticcondensed heteropolycyclic group is a carbazolyl group. A divalentnon-aromatic condensed heteropolycyclic group used herein refers to adivalent group having the same structure as the monovalent non-aromaticcondensed heteropolycyclic group.

In the present specification, at least one substituent of thesubstituted C₃-C₁₀ cycloalkylene group, the substituted C₁-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀ cycloalkenylene group,the substituted C₁-C₁₀ heterocycloalkenylene group, the substitutedC₆-C₆₀ arylene group, the substituted C₁-C₆₀ heteroarylene group, thesubstituted divalent non-aromatic condensed polycyclic group, thesubstituted divalent non-aromatic condensed heteropolycyclic group, thesubstituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group,the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxygroup, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₂-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅) and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

For example, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇);

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

where Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a furinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group.

The term “Ph” used herein refers to a phenyl group, the term “Me” usedherein refers to a methyl group, the term “Et” used herein refers to anethyl group, and the term “ter-Bu” or “Bu^(t)” used herein refers to atert-butyl group.

Hereinafter, an organic light-emitting device according to one or moreembodiments of the present invention will be described in more detailwith reference to Synthesis Examples and Examples.

SYNTHESIS EXAMPLES Synthesis Example 1 Synthesis of Compound 1

Synthesis of Intermediate 1-1

8-bromoquinoline (2.08 g, 10 mmol) was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., normal butyl lithium (4 mL, 2.5 M inhexane) was added thereto. One hour after the addition, at the sametemperature, trimethylborate (1.23 ml, 11 mmol) was added thereto. Theresulting solution was stirred for 5 hours, and then, 100 ml of 2M HClwas added thereto, and an extraction process was performed thereon threetimes by using 60 ml of ethylacetate. The obtained extraction fractionswere added up, and then dehydrated by using anhydrous magnesium sulfate,and distilled under reduced pressure. The obtained compound wasseparation-purified by silica gel column chromatography to produce 1.30g (yield 75%) of Intermediate 1-1 in the form of white solid. Theobtained compound was confirmed by LC-MS. C₉H₈BNO₂: M⁺ 173.1

Synthesis of Intermediate 1-2

1.73 g (10.0 mmol) of Intermediate 1-1, 2.02 g (10.0 mmol) of1-bromo-2-nitrobenzene, 0.58 g (0.5 mmol) of Pd(PPh₃)₃, 0.16 g (0.5mmol) of tetrabutylammonium bromide (TBAB), and 3.18 g (30.0 mmol) ofNa₂CO₃ were dissolved in 60 mL of a toluene/ethanol/H₂O (3/3/1) mixedsolution, and then, the resulting mixture was stirred at a temperatureof 80° C. for 16 hours. The obtained reaction solution was cooled toambient temperature, and then subjected to an extraction process threetimes by using 60 mL of water and 60 mL of diethylether. The organiclayer obtained therefrom was dried by using magnesium sulfate and theresidual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography to obtain 2.13 g(yield: 85%) of Intermediate 1-2. The obtained compound was identifiedby LC-MS. C₁₅H₁₀N₂O₂: M⁺ 250.1

Synthesis of Intermediate 1-3

2.50 g (10.0 mmol) of Intermediate 1-2, 3.56 g (30 mmol) of tin, and 5mL (50 mmol, conc. 36.5%) of a hydrochloric acid were dissolved in 60 mLof ethanol, and then, the resulting solution was stirred at atemperature of 100° C. for 8 hours. The obtained reaction solution wascooled to ambient temperature, and 3 g of sodium hydroxide dissolved in10 mL of water was added to a filtrate obtained by performing filtrationunder reduced pressure, and an extraction process was performed thereonthree times by using 60 mL of water and 60 mL of dichloromethane. Theorganic layer obtained therefrom was dried by using magnesium sulfateand the residual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography to obtain 1.98 g(yield of 90%) of Intermediate 1-3. The obtained compound was identifiedby LC-MS. C₁₅H₁₂N₂: M⁺ 220.1

Synthesis of Intermediate 1-4

2.20 g (10mmol) of Intermediate 1-3 and 3.66 g (20 mmol) of4-bromobenzaldehyde were dissolved in 10 mL of a trifluoroacetic acid,and then, the resulting solution was stirred in a seal tube at atemperature of 130° C. for 3 days. The obtained reaction solution wascooled at ambient temperature, and then subjected to quenching usingNaHCO₃, and then an extraction process was performed thereon three timesby using 60 mL of water and 60 mL of dichloromethane. The organic layerobtained therefrom was dried by using magnesium sulfate and the residualobtained by evaporating a solvent therefrom was separation-purified bysilica gel column chromatography to obtain 1.54 g (yield of 40%) ofIntermediate 1-4. The obtained compound was identified by LC-MS.C₂₂H₁₃BrN₂: M⁺ 384.1

Synthesis of Intermediate 1-5

Intermediate 1-4 (3.85 g, 10 mmol) was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., normal butyl lithium (4 mL, 2.5 M inhexane) was added thereto. One hour after the addition, at the sametemperature, chlorodiphenylphosphine (1.98 ml, 11 mmol) was addedthereto. At ambient temperature, the resulting mixture was stirred for 5hours, and then, water was added thereto and the resulting solution waswashed three times with 30 ml of diethylether. A diethylether layerobtained by the washing was dried by using MgSO₄, and then, dried underreduced pressure to obtain a product. Then, the product wasseparation-purified by column chromatography to obtain 3.43 g (yield of70%) of Intermediate 1-5 in the form of white solid. The obtainedcompound was confirmed by LC-MS. C₃₄H₂₃N₂P: M⁺ 490.2

Synthesis of Compound 1

4.90 g (10 mmol) of Intermediate 1-5 was dissolved in 50 ml ofdichloromethane, and then, 2 ml of 50 wt % dihydrogen peroxide aqueoussolution was added thereto, and the resulting solution was stirred atambient temperature for 2 hours. 50 ml of water was added thereto, andan extraction process was performed thereon three times by using 50 mlof dichloromethane. The collected organic layer was dried by usingmagnesium sulfate, and then, the residual obtained by evaporating asolvent therefrom was separation-purified by silica gel columnchromatography to obtain 4.80 g (yield of 95%) of Compound 1. Theobtained compound was identified by MS/FAB and ¹H NMR. C₃₄H₂₃N₂OP:M⁺cal.: 506.15, found: 506.05

¹H NMR (400 MHz, CDCl₃) δ (ppm) 9.09(d, 1H), 8.92(d, 1H), 8.69(d, 1H),8.34(d, 1H), 8.27(d, 1H), 8.05-8.00(m, 2H), 7.93(t, 1H), 7.82-7.65(m,8H), 7.53-7.39(m, 7H)

Synthesis Example 2 Synthesis of Compound 5

Synthesis of Intermediate 5-1

3.85 g of Intermediate 1-4 (10 mmol) was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., normal butyl lithium (4 mL, 2.5 M inhexane) was added thereto. One hour after the addition, at the sametemperature, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.24ml, 11 mmol) was added thereto. At ambient temperature, the resultingmixture was stirred for 5 hours, and then, water was added thereto andthe resulting solution was washed three times with 30 ml ofdiethylether. A diethylether layer obtained by the washing was dried byusing MgSO₄, and then, dried under reduced pressure to obtain a product.Then, the product was separation-purified by column chromatography toobtain 3.24 g (yield of 75%) of Intermediate 5-1 in the form of whitesolid. The obtained compound was confirmed by LC-MS. C₂₈H₂₅BN₂O₂: M⁺432.2

Synthesis of Compound 5

4.32 g (10 mmol) of Intermediate 5-1, 3.47 g (10 mmol) of Compound A,0.58 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄],and 4.14 g (30 mmol) of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O(a volumetric ratio of 2/1) mixed solution, and then, at a temperatureof 80° C., the resultant solution was stirred for 16 hours. The reactionsolution was cooled to ambient temperature, and then, 40 mL of water wasadded thereto, and an extraction process was performed thereon threetimes with 50 mL of ethylether. The collected organic layer was dried byusing magnesium sulfate, and then, the residual obtained by evaporatinga solvent therefrom was separation-purified by silica gel columnchromatography to obtain 3.72 g (yield of 65%) of Compound 5. Theobtained compound was confirmed by MS/FAB and ¹H NMR: C₄₁H₂₄N₄: M⁺cal.:572.20, found: 572.10

¹H NMR (400 MHz, CDCl₃) δ (ppm) 9.09(d, 1H), 8.92(d, 1H), 8.69(d, 1H),8.48(s, 1H), 8.36-8.30(m, 3H), 8.26(d, 1H), 8.18(s, 1H), 7.96-7.91(m,3H), 7.85-7.77(m, 3H), 7.69(d, 1H), 7.62(d, 1H), 7.53-7.45(m, 5H),7.34-7.24(m, 2H)

Synthesis Example 3 Synthesis of Compound 23

Synthesis of Intermediate 23-1

3.5 g of Intermediate 23-1 was synthesized in the same (or substantiallythe same) manner as the one used to synthesize Intermediate 1-4, exceptthat 4-bromoisoquinoline was used instead of 8-bromoquinoline. Theobtained compound was confirmed by LC-MS. C₂₂H₁₃BrN₂: M⁺ 384.0

Synthesis of Intermediate 23-2

3.85 g of Intermediate 23-1 (10 mmol) was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., normal butyl lithium (4 mL, 2.5 M inhexane) was added thereto. One hour after the addition, at the sametemperature, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.24ml, 11 mmol) was added thereto. At ambient temperature, the resultingmixture was stirred for 5 hours, and then, water was added thereto andthe resulting solution was washed three times with 30 ml ofdiethylether. A diethylether layer obtained by the washing was dried byusing MgSO₄, and then, dried under reduced pressure to obtain a product.Then, the product was separation-purified by column chromatography toobtain 3.02 g (yield of 70%) of Intermediate 23-2 in the form of whitesolid. The obtained compound was confirmed by LC-MS. C₂₈H₂₅BN₂O₂: M⁺432.2

Synthesis of Compound 23

4.32 g (10 mmol) of Intermediate 23-2, 2.68 g (10 mmol) of2-chloro-4,6-diphenyl-1,3,5-triazine, 0.58 g (0.5 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 4.14 g (30 mmol)of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O (a volumetric ratioof 2/1) mixed solution, and then, at a temperature of 80° C., theresultant solution was stirred for 16 hours. The obtained reactionsolution was cooled to ambient temperature, and then, 40 mL of water wasadded thereto, and an extraction process was performed thereon threetimes with 50 mL of ethylether. The collected organic layer was dried byusing magnesium sulfate, and then, the residual obtained by evaporatinga solvent therefrom was separation-purified by silica gel columnchromatography to obtain 3.22 g (yield of 60%) of Compound 23. Theobtained compound was confirmed by MS/FAB and ¹H NMR: C₃₇H₂₃N₅: M⁺ cal.:537.20, found: 537.10

¹H NMR (400 MHz, CDCl₃) δ (ppm) 8.92(d, 1H), 8.82-8.73(m, 7H), 8.62(d,2H), 8.54(d, 1H), 8.34(d, 1H), 8.18(d, 1H), 7.96-7.88(m, 2H),7.82-7.76(m, 2H), 7.56-7.50(m, 4H), 7.45-7.40(m, 2H)

Synthesis Example 4 Synthesis of Compound 48

Synthesis of Intermediate 48-1

3.5 g of Intermediate 48-1 was synthesized in the same (or substantiallythe same) manner as the one used to synthesize Intermediate 1-4, exceptthat 3-bromoquinoline was used instead of 8-bromoquinoline. The obtainedcompound was confirmed by LC-MS. C₂₂H₁₃BrN₂: M⁺ 384.0

Synthesis of Intermediate 48-2

3.85 g of Intermediate 48-1 (10 mmol) was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., normal butyl lithium (4 mL, 2.5 M inhexane) was added thereto. One hour after the addition, at the sametemperature, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.24ml, 11 mmol) was added thereto. At ambient temperature, the resultingmixture was stirred for 5 hours, and then, water was added thereto andthe resulting solution was washed three times with 30 ml ofdiethylether. A diethylether layer obtained by the washing was dried byusing MgSO₄, and then, dried under reduced pressure to obtain a product.Then, the product was separation-purified by column chromatography toobtain 3.24g (yield of 75%) of Intermediate 48-2 in the form of whitesolid. The obtained compound was confirmed by LC-MS. C₂₈H₂₅BN₂O₂: M⁺432.2

Synthesis of Compound 48

4.32 g (10 mmol) of Intermediate 48-2, 2.47g (10 mmol) of2-bromodibenzo[b,d]furan, 0.58 g (0.5 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 4.14 g (30 mmol)of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O (a volumetric ratioof 2/1) mixed solution, and then, at a temperature of 80° C., theresultant solution was stirred for 16 hours. The obtained reactionsolution was cooled to ambient temperature, and then, 40 mL of water wasadded thereto, and an extraction process was performed thereon threetimes with 50 mL of ethylether. The collected organic layer was dried byusing magnesium sulfate, and then, the residual obtained by evaporatinga solvent therefrom was separation-purified by silica gel columnchromatography to obtain 2.60 g (yield of 55%) of Compound 48. Theobtained compound was confirmed by MS/FAB and ¹H NMR: C₃₄H₂₀N₂O: M⁺cal.: 472.16, found: 472.06

¹H NMR (400 MHz, CDCl₃) δ (ppm) 9.19(s, 1H), 8.87(d, 1H), 8.36(d, 2H),8.14(d, 1H), 8.07-8.04(m, 2H), 7.94-7.89(m, 4H), 7.85-7.64(m, 6H),7.52-7.49(m, 1H), 7.40-7.30(m, 2H)

Synthesis Example 5 Synthesis of Compound 61

Synthesis of Intermediate 61-1

1.73 g (10.0 mmol) of Intermediate 1-1, 4.22 g (15.0 mmol) of1,4-dibromo-2-nitrobenzene, 0.58 g (0.5 mmol) of Pd(PPh₃)₃, 0.16 g (0.5mmol) of tetrabutylammonium bromide (TBAB), and 3.18 g (30.0 mmol) ofNa₂CO₃ were dissolved in 60 mL of a toluene/ethanol/H₂O (3/3/1) mixedsolution, and then, the resulting mixture was stirred at a temperatureof 80° C. for 16 hours. The obtained reaction solution was cooled toambient temperature, and then subjected to an extraction process threetimes by using 60 mL of water and 60 mL of diethylether. The organiclayer obtained therefrom was dried by using magnesium sulfate and theresidual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography to obtain 2.63 g(yield of 80%) of Intermediate 61-1. The obtained compound wasidentified by LC-MS. C₁₅H₉BrN₂O₂: M⁺ 327.9

Synthesis of Intermediate 61-2

3.29 g (10.0 mmol) of Intermediate 61-1, 3.56 g (30 mmol) of tin, and 5mL (50 mmol, conc. 36.5%) of a hydrochloric acid were dissolved in 60 mLof ethanol, and then, the resulting mixture was stirred at a temperatureof 100° C. for 8 hours. The obtained reaction solution was cooled toambient temperature, and 3 g of sodium hydroxide dissolved in 10 mL ofwater was added to a filtrate obtained by performing filtration underreduced pressure, and an extraction process was performed thereon threetimes by using 60 mL of water and 60 mL of dichloromethane. The organiclayer obtained therefrom was dried by using magnesium sulfate and theresidual obtained by evaporating a solvent therefrom wasseparation-purified by silica gel column chromatography to obtain 2.69 g(yield of 90%) of Intermediate 61-2. The obtained compound wasidentified by LC-MS. C₁₅H₁₁BrN₂: M⁺ 298.0

Synthesis of Intermediate 61-3

2.99 g (10 mmol) of Intermediate 61-2 and 2.12 g (20 mmol) ofbenzaldehyde were dissolved in 10 mL of a trifluoro acetic acid, andthen, the resulting mixture was stirred in a seal tube at a temperatureof 130° C. for 3 days. The obtained reaction solution was cooled atambient temperature, and then subjected to quenching using NaHCO₃, andthen an extraction process was performed thereon three times by using 60mL of water and 60 mL of dichloromethane. The organic layer obtainedtherefrom was dried by using magnesium sulfate and the residual obtainedby evaporating a solvent therefrom was separation-purified by silica gelcolumn chromatography to obtain 1.54g (yield of 40%) of Intermediate61-3. The obtained compound was identified by LC-MS. C₂₂H₁₃BrN₂: M⁺384.0

Synthesis of Intermediate 61-4

3.85 g (10 mmol) of Intermediate 61-3 was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., normal butyl lithium (4 mL, 2.5 M inhexane) was added thereto. One hour after the addition, at the sametemperature, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.04ml, 10 mmol) was added thereto. At ambient temperature, the resultingmixture was stirred for 5 hours, and then, water was added thereto andthe resulting solution was washed three times with 30 ml ofdiethylether. A diethylether layer obtained by the washing was dried byusing MgSO₄, and then, dried under reduced pressure to obtain a product.Then, the product was separation-purified by column chromatography toobtain 3.02 g (yield of 70%) of Intermediate 61-4 in the form of whitesolid. The obtained compound was confirmed by LC-MS. C₂₈H₂₅BN₂O₂: M⁺432.2

Synthesis of Intermediate 61-5

4.32 g (10 mmol) of Intermediate 61-4, 3.54 g (15 mmol) of1,3-dibromobenzene, 0.58 g (0.5 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 4.14 g (30 mmol)of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O (a volumetric ratioof 2/1) mixed solution, and then, at a temperature of 80° C., theresultant solution was stirred for 16 hours. The obtained reactionsolution was cooled to ambient temperature, and then, 40 mL of water wasadded thereto, and an extraction process was performed thereon threetimes with 50 mL of ethylether. The collected organic layer was dried byusing magnesium sulfate, and then, the residual obtained by evaporatinga solvent therefrom was separation-purified by silica gel columnchromatography to obtain 2.77g (yield of 60%) of Intermediate 61-5. Theobtained compound was confirmed by LC-MS. C₂₈H₁₇BrN₂: M⁺ 460.0

Synthesis of Intermediate 61-6

4.61 g (10 mmol) of Intermediate 61-5 was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., 4 ml of normal butyl lithium (2.5 Min hexane) was added thereto. One hour after the addition, at the sametemperature, chlorodiphenylphosphine (1.98 ml, 11 mmol) was addedthereto. At ambient temperature, the resulting mixture was stirred for 5hours, and then, water was added thereto and the resulting solution waswashed three times with 30 ml of diethylether. The diethylether layerwas dried by using MgSO₄, and then, dried under reduced pressure toobtain a product. Then, the product was separation-purified by columnchromatography to obtain 3.96 g (yield of 70%) of Intermediate 61-6. Theobtained compound was confirmed by LC-MS. C₄₀H₂₇N₂P: M⁺ 566.1

Synthesis of Compound 61

5.67 g (10 mmol) of Intermediate 61-6 was dissolved in 50 ml ofdichloromethane, and then, 2 ml of 50 wt % dihydrogen peroxide aqueoussolution was added thereto, and the resulting mixture was stirred atambient temperature for 2 hours. 50 ml of water was added thereto, andan extraction process was performed thereon three times by using 50 mlof dichloromethane. The collected organic layer was dried by usingmagnesium sulfate, and then, the residual obtained by evaporating asolvent therefrom was separation-purified by silica gel columnchromatography to obtain 5.53 g (yield of 95%) of Compound 61. Theobtained compound was identified by MS/FAB and ¹H NMR. C₄₀H₂₇N₂OP: M⁺cal.: 582.19, found: 582.09

¹H NMR (400 MHz, CDCl₃) δ (ppm) 9.09(d, 1H), 8.69(d, 1H), 8.40(s, 1H),8.27(d, 1H), 8.12-8.05(m, 3H), 7.97-7.97(m, 2H), 7.82-7.75(m, 2H),7.68-7.39(m, 16H)

Synthesis Example 6 Synthesis of Compound 71

Synthesis of Intermediate 71-1

4.32 g (10 mmol) of Intermediate 61-4, 5.04 g (15 mmol) of9,10-dibromoanthracene, 0.58 g (0.5 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 4.14 g (30 mmol)of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O (a volumetric ratioof 2/1) mixed solution, and then, at a temperature of 80° C., theresultant solution was stirred for 16 hours. The obtained reactionsolution was cooled to ambient temperature, and then, 40 mL of water wasadded thereto, and an extraction process was performed thereon threetimes with 50 mL of ethylether. The collected organic layer was dried byusing magnesium sulfate, and then, the residual obtained by evaporatinga solvent therefrom was separation-purified by silica gel columnchromatography to obtain 3.64 g (yield of 65%) of Intermediate 71-1. Theobtained compound was confirmed by LC-MS. C₃₆H₂₁BrN₂: M⁺ 560.0

Synthesis of Intermediate 71-2

5.61 g (10 mmol) of Intermediate 71-1 was dissolved in 30 ml of THF, andthen, at a temperature of −78° C., 4 ml of normal butyl lithium (2.5 Min hexane) was added thereto. One hour after the addition, at the sametemperature, 2.04 ml (10 mmol) of2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added thereto.At ambient temperature, the resulting mixture was stirred for 5 hours,and then, water was added thereto and the resulting solution was washedthree times with 30 ml of diethylether. The diethylether layer was driedby using MgSO₄, and then, dried under reduced pressure to obtain aproduct. Then, the product was separation-purified by columnchromatography to obtain 4.26g (yield of 70%) of Intermediate 71-2. Theobtained compound was confirmed by LC-MS. C₄₂H₃₃BN₂O₂: M⁺ 608.2

Synthesis of Compound 71

6.09 g (10 mmol) of Intermediate 71-2, 3.47 g (10 mmol) of Compound A,0.58 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄],and 4.14 g (30 mmol) of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O(a volumetric ratio of 2/1) mixed solution, and then, at a temperatureof 80° C., the resultant solution was stirred for 16 hours. The obtainedreaction solution was cooled to ambient temperature, and then, 40 mL ofwater was added thereto, and an extraction process was performed thereonthree times with 50 mL of ethylether. The collected organic layer wasdried by using magnesium sulfate, and then, the residual obtained byevaporating a solvent therefrom was separation-purified by silica gelcolumn chromatography to obtain 4.87 g (yield of 65%) of Compound 71.The obtained compound was confirmed by MS/FAB and 1H NMR: C₅₅H₃₂N₄: M⁺cal.: 748.26, found: 748.16

¹H NMR (400 MHz, CDCl₃) δ (ppm) 9.09(d, 1H), 8.94(d, 1H), 8.72(s, 1H),8.69(d, 1H), 8.48(s, 1H), 8.41-8.38(m, 2H), 8.27(d, 1H), 7.96-7.58(m,13H), 7.53-7.45(m, 5H), 7.37-7.24(m, 6H)

Synthesis Example 7 Synthesis of Compound 77

Synthesis of Intermediate 77-1

4.32 g of Intermediate 77-1 was synthesized in the same (orsubstantially the same) manner as the one used to synthesizeIntermediate 61-4, except that 4-bromoisoquinoline was used instead of8-bromoquinoline. The obtained compound was confirmed by LC-MS.C₂₈H₂₅BN₂O₂: M⁺ 432.2

Synthesis of Compound 77

6.09 g (10 mmol) of Intermediate 77-1, 2.72 g (10 mmol) of Compound B,0.58 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄],and 4.14 g (30 mmol) of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O(a volumetric ratio of 2/1) mixed solution, and then, at a temperatureof 80° C., the resultant solution was stirred for 16 hours. The obtainedreaction solution was cooled to ambient temperature, and then, 40 mL ofwater was added thereto, and an extraction process was performed thereonthree times with 50 mL of ethylether. The collected organic layer wasdried by using magnesium sulfate, and then, the residual obtained byevaporating a solvent therefrom was separation-purified by silica gelcolumn chromatography to obtain 3.23 g (yield of 65%) of Compound 77.The obtained compound was confirmed by MS/FAB and 1H NMR: C₃₅H₁₉N₃O: M⁺cal.: 497.15, found: 497.05

¹H NMR (400 MHz, CDCl₃) δ (ppm) 8.82(s, 1H), 8.73(d, 1H), 8.53(d, 1H),8.51(s, 1H), 8.44(s, 1H), 8.32(s, 1H), 7.18(d, 1H), 8.08-8.04(m, 2H),7.96-7.74(m, 6H), 7.64(d, 1H), 7.50-7.41(m, 3H)

Synthesis Example 8 Synthesis of Compound 95

Synthesis of Intermediate 95-1

4.32 g of Intermediate 95-1 was synthesized in the same (orsubstantially the same) manner as the one used to synthesizeIntermediate 61-4, except that 3-bromoquinoline was used instead of8-bromoquinoline. The obtained compound was confirmed by LC-MS.C₂₈H₂₅BN₂O₂: M⁺ 432.2

Synthesis of Compound 95

6.09g (10 mmol) of Intermediate 95-1, 2.72 g (10 mmol) of2-bromodibenzo[b,d]thiophene, 0.58 g (0.5 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 4.14 g (30 mmol)of K₂CO₃ were dissolved by using 60 mL of a THF/H₂O (a volumetric ratioof 2/1) mixed solution, and then, at a temperature of 80° C., theresultant solution was stirred for 16 hours. The obtained reactionsolution was cooled to ambient temperature, and then, 40 mL of water wasadded thereto, and an extraction process was performed thereon threetimes with 50 mL of ethylether. The collected organic layer was dried byusing magnesium sulfate, and then, the residual obtained by evaporatinga solvent therefrom was separation-purified by silica gel columnchromatography to obtain 3.17 g (yield of 65%) of Compound 95. Theobtained compound was confirmed by MS/FAB and 1H NMR: C₃₄H₂₀N₂S: M⁺cal.: 488.13, found: 488.03

¹H NMR (400 MHz, CDCl₃) δ (ppm) 9.19(s, 1H), 8.67(d, 1H), 8.49(s, 1H),8.46(s, 1H), 8.16-8.08(m, 3H), 7.96-7.93(m, 3H), 7.85-7.42(m, 10H)

Example 1

An anode was prepared by cutting a Corning 15 Ω/cm² (1200 Å) ITO glasssubstrate to a size of 50 mm×50 mm×0.7 mm, sonicating the glasssubstrate by using isopropyl alcohol and pure water for 5 minutes each,and then irradiating UV light for 30 minutes thereto and exposing toozone to clean. Then, the obtained anode was loaded onto a vacuumdeposition apparatus.

Then, 2-TNATA was vacuum deposited thereon to form a hole injectionlayer having a thickness of 600 Å, and then,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was deposited onthe hole injection layer to form a hole transport layer having athickness of 300 Å.

9,10-di-naphthalene-2-yl-anthracene (ADN), as a blue fluorescent host,and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (BDAVBi), asa blue fluorescent dopant, were co-deposited on the hole transport layerat a weight ratio of 98:2 to form an emission layer having a thicknessof 300 Å.

Then, Compound 1 was deposited on the emission layer to form an electrontransport layer having a thickness of 300 Å, and then, LiF, which is ahalogenated alkali metal, was deposited on the electron transport layerto form an electron injection layer having a thickness of 10 Å, and Alwas vacuum deposited thereon to a thickness of 3000 Å (as a cathode),thereby forming an LiF/Al electrode and completing the manufacturing ofan organic light-emitting device.

The obtained organic light-emitting device showed a driving voltage of5.03

V at the current density of 50 mA/cm², a luminescence of 3,055 cd/m²,and a current efficiency of 6.11 cd/A. At the current density of 100mA/cm², the organic light-emitting device showed a luminescence halflifespan of 355 hr.

Example 2

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 5 was used instead of Compound 1.

Example 3

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 23 was used instead of Compound1.

Example 4

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 48 was used instead of Compound1.

Example 5

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 61 was used instead of Compound1.

Example 6

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 71 was used instead of Compound1.

Example 7

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 77 was used instead of Compound1.

Example 8

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Compound 95 was used instead of Compound1.

Comparative Example 1

An organic light-emitting device was manufactured in the same (orsubstantially the same) manner as in Example 1, except that in formingthe electron transport layer, Alq3 was used instead of Compound 1. Theresulting organic light-emitting device showed a driving voltage of 7.35V at the current density of 50 mA/cm², a luminescence of 2,065 cd/m²,and a current efficiency of 4.13 cd/A. At the current density of 100mA/cm², the organic light-emitting device showed a luminescence halflifespan of 145 hr.

Results of evaluation of organic light-emitting devices according toComparative Example and Examples are shown in Table 1 below.

TABLE Half Driving Current lifespan voltage density Luminance EfficiencyEmission (hr @ Material (V) (mA/cm²) (cd/m²) (cd/A) color 100 mA/cm²)Example 1 Compound 1 5.03 50 3,055 6.11 Blue 355 hr Example 2 Compound 55.68 50 3,160 6.32 Blue 336 hr Example 3 Compound 5.35 50 3,390 6.78Blue 413 hr 23 Example 4 Compound 5.52 50 3,425 6.85 Blue 356 hr 48Example 5 Compound 5.34 50 3,165 6.33 Blue 415 hr 61 Example 6 Compound5.20 50 3,280 6.56 Blue 386 hr 71 Example 7 Compound 5.64 50 3,435 6.87Blue 399 hr 77 Example 8 Compound 5.75 50 3,125 6.25 Blue 345 hr 95Comparative Alq₃ 7.35 50 2,065 4.13 Blue 145 hr Example 1

As illustrated by the results in Table 1, when compounds represented by

Formula 1 or Formula 2 according to embodiments of the present inventionwere used as an electron transport material, the resulting organiclight-emitting devices showed 1 V or more decrease in driving voltageand a substantial increase in efficiency as compared to the organiclight-emitting device in which Alq₃ was used as an electron transportmaterial. In other words, compounds according to embodiments of thepresent invention showed excellent I-V_L characteristics. These resultsillustrate that compounds according to embodiments of the presentinvention are excellent for use as an electron transport material.

Compounds according to embodiments of the present invention have anexcellent electron transport capability. An organic light-emittingdevice manufactured using such compounds has high efficiency, lowvoltage, high brightness, and a long lifespan.

It should be understood that the embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

As used herein, expressions such as “at least one of”, “one of,” and“one selected from” when preceding a list of elements, modify the entirelist of elements and do not modify the individual elements of the list.Further, the use of “may” when describing embodiments of the presentinvention refers to “one or more embodiments of the present invention.”

In addition, as used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. As used herein, the term “substantially,”“about,” and similar terms are used as terms of approximation and not asterms of degree, and are intended to account for the inherent deviationsin measured or calculated values that would be recognized by those ofordinary skill in the art.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein. All suchranges are intended to be inherently described in this specificationsuch that amending to expressly recite any such subranges would complywith the requirements of 35 U.S.C. §112, first paragraph, and 35 U.S.C.§132(a).

While one or more embodiments have been described with reference to thedrawing, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope of the present disclosure as definedby the following claims and equivalents thereof.

What is claimed is:
 1. A compound represented by Formula 1 or Formula 2:

wherein in Formulae 1 and 2, R₁ to R₄ are each independently selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —P(═O)R₁₁R₁₂, and —P(═S)R₁₃R₁₄; L₁ to L₄ areeach independently selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group; X₁ to X₁₂ are eachindependently CR₂₁ or N; at least one selected from X₁ to X₁₂ is N; R₁₁to R₁₄, and R₂₁ are each independently selected from a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromaticcondensed polycyclic group, and a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group; l, m, n, and oare each independently an integer selected from 1 to 5; a1, a2, a3, anda4 are each independently an integer selected from 0 to 3, and when a1,a2, a3, and a4 are each independently 2 or more, respective L₁s to L₄sare each independently identical to or different from each other; and atleast one of substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group,substituted monovalent non-aromatic condensed heteropolycyclic group,C₃-C₁₀ cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylenegroup, substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, and substituted divalentnon-aromatic condensed heteropolycyclic group is selected from:deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and—B(Q₁₆)(Q₁₇); a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₂-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₂-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅) and —B(Q₂₆)(Q₂₇); and —N(Q₃₁)(Q₃₂),—Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇); wherein Q₁₁ to Q₁₇, Q₂₁ to Q₂₇,and Q₃₁ to Q₃₇ are each independently selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.
 2. The compound of claim 1, wherein at least oneselected from X₁ and X₆ in Formula 1 is N.
 3. The compound of claim 1,wherein the compound represented by Formula 1 is a compound representedby Formula 3:


4. The compound of claim 1, wherein the compound represented by Formula1 is a compound represented by Formula 4:


5. The compound of claim 1, wherein the compound represented by Formula2 is a compound represented by Formula 5 below:


6. The compound of claim 1, wherein R₁ to R₄ are each independentlyselected from hydrogen, deuterium, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group.
 7. The compound of claim1, wherein R₁ to R₄ are each independently selected from hydrogen,deuterium, a phenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group,a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, afurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group; and a phenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a furinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a pentalenyl group, an indenylgroup, a naphthyl group, an azulenyl group, a heptalenyl group, anindacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a furinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group.
 8. The compoundof claim 1, wherein L₁ to L₄ are each independently selected from asubstituted or unsubstituted C₆-C₆₀ arylene group, a substituted orunsubstituted C₁-C₆₀ heteroarylene group, a substituted or unsubstituteddivalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group. 9.The compound of claim 1, wherein L₁ to L₄ are each independentlyselected from a phenylene group, a pentalenylene group, an indenylenegroup, a naphthylene group, an azulenylene group, a heptalenylene group,an indacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a furinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group; and aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a furinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group,eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a pherylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a furinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.
 10. Thecompound of claim 1, wherein R₁ to R₄ are each independently selectedfrom hydrogen, deuterium, and groups represented by Formulae 2a to 2f:

wherein in Formulae 2a to 2f, H₁ is NR₂₁, O, or S; R₁₁, R₁₂, R₂₁, Z₁,and Z₂ are each independently selected from hydrogen atom, deuterium, ahalogen group, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, a substituted or unsubstituted C₁-C₂₀ alkyl group, asubstituted or unsubstituted C₆-C₂₀ aryl group, a substituted orunsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;p is an integer selected from 1 to 9, and when p is 2 or more, theplurality of Z₁(s) are identical to or different from each other; and *indicates a binding site.
 11. The compound of claim 1, wherein L₁ to L₄are each independently selected from one of Formulae 3a to 3c:

wherein in Formulae 3a to 3c, Z₁ is selected from hydrogen atom,deuterium, a halogen group, a cyano group, a nitro group, a hydroxylgroup, a carboxyl group, a substituted or unsubstituted C₁-C₂₀ alkylgroup, a substituted or unsubstituted C₆-C₂₀ aryl group, a substitutedor unsubstituted C₁-C₂₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;and * indicates a binding site.
 12. The compound of claim 1, wherein thecompound represented by Formula 1 or Formula 2 is any one selected fromCompounds 1-102:


13. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode, the organic layercomprising an emission layer, wherein the organic layer comprises thecompound represented by Formula 1 or Formula 2 of claim
 1. 14. Theorganic light-emitting device of claim 13, wherein the organic layer isformed by a wet process.
 15. The organic light-emitting device of claim13, wherein the first electrode is an anode, the second electrode is acathode, and the organic layer comprises: i) a hole transport regionbetween the first electrode and the emission layer, the hole transportregion comprising at least one selected from a hole injection layer, ahole transport layer, and an electron blocking layer, and ii) anelectron transport region between the emission layer and the secondelectrode, the electron transport region comprising an electrontransport layer and at least one selected from a hole blocking layer andan electron injection layer.
 16. The organic light-emitting device ofclaim 15, wherein the electron transport region comprises the compoundrepresented by Formula 1 or Formula
 2. 17. The organic light-emittingdevice of claim 15, wherein the electron transport layer comprises thecompound represented by Formula 1 or Formula
 2. 18. The organiclight-emitting device of claim 15, wherein the hole transport regioncomprises a charge-generating material.
 19. The organic light-emittingdevice of claim 15, wherein the hole transport region comprises ap-dopant.
 20. The organic light-emitting device of claim 15, wherein thehole transport region comprises one selected from a quinone derivative,a metal oxide, and a cyano group-containing compound.
 21. The organiclight-emitting device of claim 15, wherein the electron transport regioncomprises a metal complex.
 22. The organic light-emitting device ofclaim 21, wherein the metal complex is an Li complex.
 23. The organiclight-emitting device of claim 21, wherein the metal complex is alithium quinolate (LiQ).
 24. The organic light-emitting device of claim21, wherein the metal complex is compound ET-D2:


25. A flat display apparatus comprising the organic light-emittingdevice of claim 13, wherein the first electrode of the organiclight-emitting device is electrically connected to a source electrode ora drain electrode of a thin film transistor.